


Express Yourself

by 50shadesofsubtext



Series: SPN AU and Trope Bingo [2]
Category: Supernatural
Genre: Bar Hopping, Crossdressing, Dean in Panties, Disney Princess/Princess!au, Drag Queen Dean Winchester, Drag Queens, F/F, F/M, Gay Bar, Genderbending, Halloween, Halloween Squad Costumes, M/M, Public Hand Jobs, SPN AU Bingo, disney costumes, drag kings
Language: English
Status: Completed
Published: 2017-12-11
Updated: 2017-12-11
Packaged: 2019-02-13 16:12:00
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,301
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/12987690
Author URL: https://archiveofourown.org/users/50shadesofsubtext/pseuds/50shadesofsubtext
Summary: Dean and the squad cross dress Halloween in full Disney drag and bar hop around town.Fill for my SPN AU and Trope Bingo for the square Disney princess/princess!au.





	Express Yourself

**Author's Note:**

> The title is from Madonna’s song of the same name.

The makeup tutorial played on the phone in front of Dean, and he stared into the mirror, matching each brush stroke perfectly.

Everything was going to be perfect tonight.

“Your majesty, we’re going to be late!” Sam yelled from the bottom of the stairs. It was easy for him to say, he was ready to go an hour ago.

“Hold on. I’m almost done!”

Dean stepped back from the mirror and looked at the long blond wig that fell around his shoulders. He double checked the makeup one last time and unbuttoned the flannel shirt that protected the silvery-blue dress while he got ready.

He smiled and kissed the mirror, leaving a bright pink set of lips on the mirror. He’d never understood why girls did that in movies, but he smiled at the imprint. He understood now. It gave him a burst of power and pride.

He grabbed his heels in one hand and raced down the stairs. Sam made a fierce looking Cinderella and Cas made such a cute Anna that Dean couldn’t resist leaning in for a kiss.

Jess came into the doorway as Sam called that they were ready. Her hair was swept back, and the Prince Charming outfit fit her perfectly.

This was going to be the greatest Halloween they ever had.

The rest of the crew met them at the Roadhouse. Ash as Belle to Jo’s Prince Adam, Benny as Ariel to Andrea’s Prince Eric and Charlie and Dorothy as Olaf and Sven. Kevin even dressed up as Snow White, likely due to Charlie’s insistence, and Meg and Ruby looked fabulous as Peter Pan and Captain Hook.

Jody dressed as Aladdin, Claire as the Genie, and Alex as the Sultan. Alex glared at the group for making her wear such a ridiculous outfit and stood by the door, waiting to go.

Ellen came out from behind the bar with her sword and shield, red cloak flowing over down her back to hide the blue underneath. “He won’t come out.”

They let out a laugh, and Dean cried out in a high-pitched voice, “Sleeping Beauty, do you need your true love’s kiss to wake you up?”

A loud gruff came from behind the door, and it swung open revealing Bobby in a flowing pink dress, blond wig, and tiara.

“Bobby,” Dean said with a smile, “did you not watch the drag videos we sent you? We gave you tutorials on this.”

“I ain’t never wore makeup in my life, boy, and I ain’t gonna start because of this stupid idea.”

Dean let out a laugh and promised Bobby he would get him for this.

They took pictures together before Sam looked down at his watch. “Guys, it’s almost ten, we should probably go.” Ellen and Bobby grumbled about making them stay up so late, and Jo reminded them they were leaving so early because of them.

They piled into the cars and drove into town. They found parking blocks from the main strip of bars and walked to the first bar, Bobby’s choice. It was a country bar, and everyone wore a cowboy hat. The patrons looked at the group like they were from outer-space. Bobby and Ellen ordered drinks and Jody wanted to try it out for their sake. Jo didn’t want to leave her mom, so she hung back with Ash, and the rest of group took one look at the place and walked back out the door.

They went to the next bar, Charlie and Dorothy's choice. Dean laughed at the lesbians that admired them. They got appreciative looks on their way to the bar, and everyone in the group got a beer paid for. Kevin was surrounded by a group of butches that looked like they could devour the kid and Alex and Claire found a group of women that didn’t bother changing out of flannels for the holiday. By the time they were ready to leave, Ruby and Meg were nowhere to be found.

Dean felt the light buzz fill him up. He wrapped an arm around Cas’ waist as they walked to Sam and Jess’ choice. They only served light beer and zero calorie mixed drinks with sprigs of vegetables in them, and a faint smell of weed came from the back.

The next bar was for Claire and Alex, a college bar with appetizers in huge portions. Cas ordered a plate of nachos for them, and it took everyone to finish the enormous pile. They went to a sports bar next for Benny and then a weird bar on Kevin’s recommendation that had a four-piece orchestra and overpriced drinks with fancy sounding names.

Finally, Dean ended up at his bar. The smell of sweaty men and spilled beer hit his nose, and he smiled, pulling Cas close and grinding their hips together. The extra fabric from the petticoats and skirts blocked the grind of their erections. Cas pulled Dean onto the middle of the dance floor. The go-go dancers in cages lit the room around them, and Dean matched his grind to the strobe light pulsing above them.

Dean wasn’t drunk, not quite, but the next shot would do him in. Cas looked the same like he could only focus on Dean, and the rest of the world was just background.

Dean pulled him even closer and shouted to be heard over the music, “You know I only have a pair of blue lace panties under this dress?”

Cas groaned against his neck and yelled back, “Why did we even leave the house tonight?”

Cas made a good point. They could have just stayed in and fucked the night away. Maybe they should have. And yet, Cas in full princess drag was not a sight to be missed. The way his shoulders were bare, straps barely holding on to the top of his arms. The way the dress perfectly cupped his fake tits with the sweetheart neckline. He wouldn’t have missed this for the world.

He mouthed along Cas’ neckline nipping at the skin he could reach. Cas was beautiful.

Jo must have caught up with them because she was the one that found them later after Dean pushed Cas against a wall and found that it was only slightly more difficult to reach a hand up a full-length skirt.

“We're moving on,” she yelled over the music, and Dean felt Cas’ head nod from where his lips found permanent residence on Cas’ neck.

“We should find a hotel room,” Cas told him. He was right, of course, but Dean shook his head.

“I’m not leaving here until I make you cum into the glitter on this floor.”

Cas moaned again and pushed the front of Dean’s dress up, finally cupping the erection trapped in the tight lace. “Good luck,” Cas yelled as he rolled Dean’s balls in his hand.

It was Dean’s favorite race, who could get off who faster. Dean swiped two fingers through the pre-come on Cas’ head and reached further back, pressing into Cas’ hole. Cas shuttered, and Dean added the second finger, opening him with so little lubricant that the fingers fought the friction. It was rough, just like Cas liked it and it was only seconds before Cas shot his load onto the underside of the dress and the glitter below them.

“Dirty boy,” Dean chided, “You weren’t even wearing any underwear under that pretty dress of yours. No way you could have beat me.”

Cas just laughed and flicked his wrist against the underside of Dean’s head. It only took a few quick jerks against the fabric before Dean let loose, cum soaking the panties.

Cas smiled at his victory and wiped his hand on Dean’s thigh. Dean kissed the smirk off Cas’ face.

This was the greatest Halloween they ever had.


End file.
